From 10b1e211fe7158437cf6ac60e8f436829d7cd9a3 Mon Sep 17 00:00:00 2001
From: Peyton Montei <peyton@entire.io>
Date: Fri, 13 Feb 2026 16:57:25 -0800
Subject: [PATCH 1/2] Replace ApplyCommonActions with ActionHandler interface

---
 cmd/entire/cli/hooks.go                       |   2 +-
 cmd/entire/cli/hooks_claudecode_handlers.go   |   4 +-
 cmd/entire/cli/session/phase.go               |  56 +++--
 cmd/entire/cli/session/phase_test.go          | 209 ++++++++++--------
 .../cli/strategy/manual_commit_hooks.go       | 143 +++++++-----
 .../cli/strategy/phase_postcommit_test.go     |   7 +-
 cmd/entire/cli/strategy/session_state.go      |  19 +-
 cmd/entire/cli/strategy/session_state_test.go |  31 +++
 cmd/entire/cli/strategy/strategy.go           |   2 +-
 9 files changed, 287 insertions(+), 186 deletions(-)

diff --git a/cmd/entire/cli/hooks.go b/cmd/entire/cli/hooks.go
index 005ae8c5c..1356f9733 100644
--- a/cmd/entire/cli/hooks.go
+++ b/cmd/entire/cli/hooks.go
@@ -284,7 +284,7 @@ func handleSessionStartCommon() error {
 	if state, loadErr := strategy.LoadSessionState(input.SessionID); loadErr != nil {
 		fmt.Fprintf(os.Stderr, "Warning: failed to load session state on start: %v\n", loadErr)
 	} else if state != nil {
-		strategy.TransitionAndLog(state, session.EventSessionStart, session.TransitionContext{})
+		strategy.TransitionAndLog(state, session.EventSessionStart, session.TransitionContext{}, session.NoOpActionHandler{})
 		if saveErr := strategy.SaveSessionState(state); saveErr != nil {
 			fmt.Fprintf(os.Stderr, "Warning: failed to update session state on start: %v\n", saveErr)
 		}
diff --git a/cmd/entire/cli/hooks_claudecode_handlers.go b/cmd/entire/cli/hooks_claudecode_handlers.go
index b2fade179..9d084d893 100644
--- a/cmd/entire/cli/hooks_claudecode_handlers.go
+++ b/cmd/entire/cli/hooks_claudecode_handlers.go
@@ -748,7 +748,7 @@ func transitionSessionTurnEnd(sessionID string) {
 	if turnState == nil {
 		return
 	}
-	strategy.TransitionAndLog(turnState, session.EventTurnEnd, session.TransitionContext{})
+	strategy.TransitionAndLog(turnState, session.EventTurnEnd, session.TransitionContext{}, session.NoOpActionHandler{})
 
 	// Always dispatch to strategy for turn-end handling. The strategy reads
 	// work items from state (e.g. TurnCheckpointIDs), not the action list.
@@ -774,7 +774,7 @@ func markSessionEnded(sessionID string) error {
 		return nil // No state file, nothing to update
 	}
 
-	strategy.TransitionAndLog(state, session.EventSessionStop, session.TransitionContext{})
+	strategy.TransitionAndLog(state, session.EventSessionStop, session.TransitionContext{}, session.NoOpActionHandler{})
 
 	now := time.Now()
 	state.EndedAt = &now
diff --git a/cmd/entire/cli/session/phase.go b/cmd/entire/cli/session/phase.go
index 6b5b9fc46..dda33769a 100644
--- a/cmd/entire/cli/session/phase.go
+++ b/cmd/entire/cli/session/phase.go
@@ -249,17 +249,31 @@ func transitionFromEnded(event Event, ctx TransitionContext) TransitionResult {
 	}
 }
 
-// ApplyCommonActions applies the common (non-strategy-specific) actions from a
-// TransitionResult to the given State. It updates Phase, LastInteractionTime,
-// and EndedAt as indicated by the transition.
-//
-// Returns the subset of actions that require strategy-specific handling
-// (e.g., ActionCondense, ActionWarnStaleSession).
-// The caller is responsible for dispatching those.
-func ApplyCommonActions(state *State, result TransitionResult) []Action {
+// ActionHandler defines strategy-specific side effects for state transitions.
+// The compiler enforces that every strategy-specific action has a handler.
+type ActionHandler interface {
+	HandleCondense(state *State) error
+	HandleCondenseIfFilesTouched(state *State) error
+	HandleDiscardIfNoFiles(state *State) error
+	HandleWarnStaleSession(state *State) error
+}
+
+// NoOpActionHandler is a default ActionHandler where all methods are no-ops.
+// Embed this in handler structs to only override the methods you need.
+type NoOpActionHandler struct{}
+
+func (NoOpActionHandler) HandleCondense(_ *State) error               { return nil }
+func (NoOpActionHandler) HandleCondenseIfFilesTouched(_ *State) error { return nil }
+func (NoOpActionHandler) HandleDiscardIfNoFiles(_ *State) error       { return nil }
+func (NoOpActionHandler) HandleWarnStaleSession(_ *State) error       { return nil }
+
+// ApplyTransition applies a TransitionResult to state: sets the new phase,
+// handles common actions internally, and calls the ActionHandler for
+// strategy-specific actions. Returns on the first handler error, leaving
+// subsequent actions unexecuted.
+func ApplyTransition(state *State, result TransitionResult, handler ActionHandler) error {
 	state.Phase = result.NewPhase
 
-	var remaining []Action
 	for _, action := range result.Actions {
 		switch action {
 		case ActionUpdateLastInteraction:
@@ -267,13 +281,27 @@ func ApplyCommonActions(state *State, result TransitionResult) []Action {
 			state.LastInteractionTime = &now
 		case ActionClearEndedAt:
 			state.EndedAt = nil
-		case ActionCondense, ActionCondenseIfFilesTouched, ActionDiscardIfNoFiles,
-			ActionWarnStaleSession:
-			// Strategy-specific actions — pass through to caller.
-			remaining = append(remaining, action)
+		case ActionCondense:
+			if err := handler.HandleCondense(state); err != nil {
+				return fmt.Errorf("%s: %w", action, err)
+			}
+		case ActionCondenseIfFilesTouched:
+			if err := handler.HandleCondenseIfFilesTouched(state); err != nil {
+				return fmt.Errorf("%s: %w", action, err)
+			}
+		case ActionDiscardIfNoFiles:
+			if err := handler.HandleDiscardIfNoFiles(state); err != nil {
+				return fmt.Errorf("%s: %w", action, err)
+			}
+		case ActionWarnStaleSession:
+			if err := handler.HandleWarnStaleSession(state); err != nil {
+				return fmt.Errorf("%s: %w", action, err)
+			}
+		default:
+			return fmt.Errorf("unhandled action: %s", action)
 		}
 	}
-	return remaining
+	return nil
 }
 
 // MermaidDiagram generates a Mermaid state diagram from the transition table.
diff --git a/cmd/entire/cli/session/phase_test.go b/cmd/entire/cli/session/phase_test.go
index 541308497..60c022aba 100644
--- a/cmd/entire/cli/session/phase_test.go
+++ b/cmd/entire/cli/session/phase_test.go
@@ -1,6 +1,7 @@
 package session
 
 import (
+	"errors"
 	"testing"
 	"time"
 
@@ -360,179 +361,191 @@ func TestTransition_all_phase_event_combinations_are_defined(t *testing.T) {
 	}
 }
 
-func TestApplyCommonActions_SetsPhase(t *testing.T) {
+func TestMermaidDiagram(t *testing.T) {
 	t.Parallel()
 
-	state := &State{Phase: PhaseIdle}
-	result := TransitionResult{
-		NewPhase: PhaseActive,
-		Actions:  []Action{ActionUpdateLastInteraction},
-	}
+	diagram := MermaidDiagram()
+
+	// Verify the diagram contains expected state declarations.
+	assert.Contains(t, diagram, "stateDiagram-v2")
+	assert.Contains(t, diagram, "IDLE")
+	assert.Contains(t, diagram, "ACTIVE")
+	assert.Contains(t, diagram, "ENDED")
+	assert.NotContains(t, diagram, "ACTIVE_COMMITTED")
 
-	remaining := ApplyCommonActions(state, result)
+	// Verify key transitions are present.
+	assert.Contains(t, diagram, "idle --> active")
+	assert.Contains(t, diagram, "active --> active") // ACTIVE+GitCommit stays ACTIVE
+	assert.Contains(t, diagram, "ended --> idle")
+	assert.Contains(t, diagram, "ended --> active")
 
-	assert.Equal(t, PhaseActive, state.Phase)
-	assert.Empty(t, remaining, "UpdateLastInteraction should be consumed")
+	// Verify actions appear in labels.
+	assert.Contains(t, diagram, "Condense")
+	assert.Contains(t, diagram, "ClearEndedAt")
+	assert.Contains(t, diagram, "WarnStaleSession")
+	assert.NotContains(t, diagram, "MigrateShadowBranch")
 }
 
-func TestApplyCommonActions_UpdatesLastInteractionTime(t *testing.T) {
-	t.Parallel()
+// mockActionHandler records which handler methods were called.
+type mockActionHandler struct {
+	condenseCalled               bool
+	condenseIfFilesTouchedCalled bool
+	discardIfNoFilesCalled       bool
+	warnStaleSessionCalled       bool
+	returnErr                    error
+}
 
-	state := &State{Phase: PhaseIdle}
-	before := time.Now()
+func (m *mockActionHandler) HandleCondense(_ *State) error {
+	m.condenseCalled = true
+	return m.returnErr
+}
 
-	result := TransitionResult{
-		NewPhase: PhaseActive,
-		Actions:  []Action{ActionUpdateLastInteraction},
-	}
+func (m *mockActionHandler) HandleCondenseIfFilesTouched(_ *State) error {
+	m.condenseIfFilesTouchedCalled = true
+	return m.returnErr
+}
 
-	_ = ApplyCommonActions(state, result)
+func (m *mockActionHandler) HandleDiscardIfNoFiles(_ *State) error {
+	m.discardIfNoFilesCalled = true
+	return m.returnErr
+}
 
-	require.NotNil(t, state.LastInteractionTime)
-	assert.False(t, state.LastInteractionTime.Before(before),
-		"LastInteractionTime should be >= test start time")
+func (m *mockActionHandler) HandleWarnStaleSession(_ *State) error {
+	m.warnStaleSessionCalled = true
+	return m.returnErr
 }
 
-func TestApplyCommonActions_ClearsEndedAt(t *testing.T) {
+func TestApplyTransition_SetsPhaseAndHandlesCommonActions(t *testing.T) {
 	t.Parallel()
 
-	endedAt := time.Now().Add(-time.Hour)
-	state := &State{
-		Phase:   PhaseEnded,
-		EndedAt: &endedAt,
-	}
-
+	state := &State{Phase: PhaseIdle}
+	handler := &mockActionHandler{}
 	result := TransitionResult{
-		NewPhase: PhaseIdle,
-		Actions:  []Action{ActionClearEndedAt},
+		NewPhase: PhaseActive,
+		Actions:  []Action{ActionUpdateLastInteraction},
 	}
 
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Nil(t, state.EndedAt, "EndedAt should be cleared")
-	assert.Equal(t, PhaseIdle, state.Phase)
-	assert.Empty(t, remaining, "ClearEndedAt should be consumed")
+	require.NoError(t, err)
+	assert.Equal(t, PhaseActive, state.Phase)
+	require.NotNil(t, state.LastInteractionTime)
+	assert.False(t, handler.condenseCalled)
 }
 
-func TestApplyCommonActions_PassesThroughStrategyActions(t *testing.T) {
+func TestApplyTransition_CallsHandlerForCondense(t *testing.T) {
 	t.Parallel()
 
 	state := &State{Phase: PhaseActive}
+	handler := &mockActionHandler{}
 	result := TransitionResult{
 		NewPhase: PhaseIdle,
 		Actions:  []Action{ActionCondense, ActionUpdateLastInteraction},
 	}
 
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Equal(t, []Action{ActionCondense}, remaining,
-		"ActionCondense should be passed through to caller")
+	require.NoError(t, err)
+	assert.True(t, handler.condenseCalled)
 	assert.Equal(t, PhaseIdle, state.Phase)
 	require.NotNil(t, state.LastInteractionTime)
 }
 
-func TestApplyCommonActions_MultipleStrategyActions(t *testing.T) {
+func TestApplyTransition_CallsHandlerForCondenseIfFilesTouched(t *testing.T) {
 	t.Parallel()
 
-	state := &State{Phase: PhaseActive}
+	state := &State{Phase: PhaseEnded}
+	handler := &mockActionHandler{}
 	result := TransitionResult{
-		NewPhase: PhaseActive,
-		Actions:  []Action{ActionCondense, ActionUpdateLastInteraction},
+		NewPhase: PhaseEnded,
+		Actions:  []Action{ActionCondenseIfFilesTouched, ActionUpdateLastInteraction},
 	}
 
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Equal(t, []Action{ActionCondense}, remaining)
-	assert.Equal(t, PhaseActive, state.Phase)
+	require.NoError(t, err)
+	assert.True(t, handler.condenseIfFilesTouchedCalled)
 }
 
-func TestApplyCommonActions_WarnStaleSessionPassedThrough(t *testing.T) {
+func TestApplyTransition_CallsHandlerForDiscardIfNoFiles(t *testing.T) {
 	t.Parallel()
 
-	state := &State{Phase: PhaseActive}
+	state := &State{Phase: PhaseEnded}
+	handler := &mockActionHandler{}
 	result := TransitionResult{
-		NewPhase: PhaseActive,
-		Actions:  []Action{ActionWarnStaleSession},
+		NewPhase: PhaseEnded,
+		Actions:  []Action{ActionDiscardIfNoFiles, ActionUpdateLastInteraction},
 	}
 
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Equal(t, []Action{ActionWarnStaleSession}, remaining)
+	require.NoError(t, err)
+	assert.True(t, handler.discardIfNoFilesCalled)
 }
 
-func TestApplyCommonActions_NoActions(t *testing.T) {
+func TestApplyTransition_CallsHandlerForWarnStaleSession(t *testing.T) {
 	t.Parallel()
 
-	state := &State{Phase: PhaseIdle}
+	state := &State{Phase: PhaseActive}
+	handler := &mockActionHandler{}
 	result := TransitionResult{
-		NewPhase: PhaseIdle,
-		Actions:  nil,
+		NewPhase: PhaseActive,
+		Actions:  []Action{ActionWarnStaleSession},
 	}
 
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Nil(t, remaining)
-	assert.Equal(t, PhaseIdle, state.Phase)
+	require.NoError(t, err)
+	assert.True(t, handler.warnStaleSessionCalled)
 }
 
-func TestApplyCommonActions_EndedToActiveTransition(t *testing.T) {
+func TestApplyTransition_ClearsEndedAt(t *testing.T) {
 	t.Parallel()
 
 	endedAt := time.Now().Add(-time.Hour)
-	state := &State{
-		Phase:   PhaseEnded,
-		EndedAt: &endedAt,
+	state := &State{Phase: PhaseEnded, EndedAt: &endedAt}
+	handler := &mockActionHandler{}
+	result := TransitionResult{
+		NewPhase: PhaseIdle,
+		Actions:  []Action{ActionClearEndedAt},
 	}
 
-	// Simulate ENDED → ACTIVE transition (EventTurnStart)
-	result := Transition(PhaseEnded, EventTurnStart, TransitionContext{})
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
-	assert.Equal(t, PhaseActive, state.Phase)
-	assert.Nil(t, state.EndedAt, "EndedAt should be cleared on re-entry")
-	require.NotNil(t, state.LastInteractionTime)
-	assert.Empty(t, remaining, "all actions should be consumed")
+	require.NoError(t, err)
+	assert.Nil(t, state.EndedAt)
 }
 
-func TestApplyCommonActions_EndedToIdleOnSessionStart(t *testing.T) {
+func TestApplyTransition_ReturnsHandlerError(t *testing.T) {
 	t.Parallel()
 
-	endedAt := time.Now().Add(-time.Hour)
-	state := &State{
-		Phase:   PhaseEnded,
-		EndedAt: &endedAt,
+	state := &State{Phase: PhaseActive}
+	handler := &mockActionHandler{returnErr: errors.New("condense failed")}
+	result := TransitionResult{
+		NewPhase: PhaseIdle,
+		Actions:  []Action{ActionCondense, ActionUpdateLastInteraction},
 	}
 
-	// Simulate ENDED → IDLE transition (EventSessionStart re-entry)
-	result := Transition(PhaseEnded, EventSessionStart, TransitionContext{})
-	remaining := ApplyCommonActions(state, result)
+	err := ApplyTransition(state, result, handler)
 
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "condense failed")
 	assert.Equal(t, PhaseIdle, state.Phase)
-	assert.Nil(t, state.EndedAt, "EndedAt should be cleared on session re-entry")
-	assert.Empty(t, remaining, "only ClearEndedAt, which is consumed")
 }
 
-func TestMermaidDiagram(t *testing.T) {
+func TestApplyTransition_StopsOnFirstHandlerError(t *testing.T) {
 	t.Parallel()
 
-	diagram := MermaidDiagram()
-
-	// Verify the diagram contains expected state declarations.
-	assert.Contains(t, diagram, "stateDiagram-v2")
-	assert.Contains(t, diagram, "IDLE")
-	assert.Contains(t, diagram, "ACTIVE")
-	assert.Contains(t, diagram, "ENDED")
-	assert.NotContains(t, diagram, "ACTIVE_COMMITTED")
+	state := &State{Phase: PhaseActive}
+	handler := &mockActionHandler{returnErr: errors.New("condense failed")}
+	result := TransitionResult{
+		NewPhase: PhaseIdle,
+		Actions:  []Action{ActionCondense, ActionWarnStaleSession},
+	}
 
-	// Verify key transitions are present.
-	assert.Contains(t, diagram, "idle --> active")
-	assert.Contains(t, diagram, "active --> active") // ACTIVE+GitCommit stays ACTIVE
-	assert.Contains(t, diagram, "ended --> idle")
-	assert.Contains(t, diagram, "ended --> active")
+	err := ApplyTransition(state, result, handler)
 
-	// Verify actions appear in labels.
-	assert.Contains(t, diagram, "Condense")
-	assert.Contains(t, diagram, "ClearEndedAt")
-	assert.Contains(t, diagram, "WarnStaleSession")
-	assert.NotContains(t, diagram, "MigrateShadowBranch")
+	require.Error(t, err)
+	assert.True(t, handler.condenseCalled)
+	assert.False(t, handler.warnStaleSessionCalled, "should stop on first error")
 }
diff --git a/cmd/entire/cli/strategy/manual_commit_hooks.go b/cmd/entire/cli/strategy/manual_commit_hooks.go
index a2bc4dcf8..c30ddd62a 100644
--- a/cmd/entire/cli/strategy/manual_commit_hooks.go
+++ b/cmd/entire/cli/strategy/manual_commit_hooks.go
@@ -462,6 +462,69 @@ func (s *ManualCommitStrategy) handleAmendCommitMsg(logCtx context.Context, comm
 //
 // Shadow branches are only deleted when ALL sessions sharing the branch are non-active
 // and were condensed during this PostCommit.
+
+// postCommitActionHandler implements session.ActionHandler for PostCommit.
+// Each session in the loop gets its own handler with per-session context.
+// Handler methods use the *State parameter from ApplyTransition (same pointer
+// as the state being transitioned) rather than capturing state separately.
+type postCommitActionHandler struct {
+	s                      *ManualCommitStrategy
+	logCtx                 context.Context
+	repo                   *git.Repository
+	checkpointID           id.CheckpointID
+	head                   *plumbing.Reference
+	commit                 *object.Commit
+	newHead                string
+	shadowBranchName       string
+	shadowBranchesToDelete map[string]struct{}
+	committedFileSet       map[string]struct{}
+	hasNew                 bool
+
+	// Output: set by handler methods, read by caller after TransitionAndLog.
+	condensed bool
+}
+
+func (h *postCommitActionHandler) HandleCondense(state *session.State) error {
+	// For ACTIVE sessions, any commit during the turn is session-related.
+	// For IDLE/ENDED sessions (e.g., carry-forward), also require that the
+	// committed files overlap with the session's remaining files AND have
+	// matching content — otherwise an unrelated commit (or a commit with
+	// completely replaced content) would incorrectly get this session's checkpoint.
+	shouldCondense := h.hasNew
+	if shouldCondense && !state.Phase.IsActive() {
+		shouldCondense = filesOverlapWithContent(h.repo, h.shadowBranchName, h.commit, state.FilesTouched)
+	}
+	if shouldCondense {
+		h.condensed = h.s.condenseAndUpdateState(h.logCtx, h.repo, h.checkpointID, state, h.head, h.shadowBranchName, h.shadowBranchesToDelete, h.committedFileSet)
+	} else {
+		h.s.updateBaseCommitIfChanged(h.logCtx, state, h.newHead)
+	}
+	return nil
+}
+
+func (h *postCommitActionHandler) HandleCondenseIfFilesTouched(state *session.State) error {
+	if len(state.FilesTouched) > 0 && h.hasNew {
+		h.condensed = h.s.condenseAndUpdateState(h.logCtx, h.repo, h.checkpointID, state, h.head, h.shadowBranchName, h.shadowBranchesToDelete, h.committedFileSet)
+	} else {
+		h.s.updateBaseCommitIfChanged(h.logCtx, state, h.newHead)
+	}
+	return nil
+}
+
+func (h *postCommitActionHandler) HandleDiscardIfNoFiles(state *session.State) error {
+	if len(state.FilesTouched) == 0 {
+		logging.Debug(h.logCtx, "post-commit: skipping empty ended session (no files to condense)",
+			slog.String("session_id", state.SessionID),
+		)
+	}
+	h.s.updateBaseCommitIfChanged(h.logCtx, state, h.newHead)
+	return nil
+}
+
+func (h *postCommitActionHandler) HandleWarnStaleSession(_ *session.State) error {
+	// Not produced by EventGitCommit; no-op for exhaustiveness.
+	return nil
+}
 // During rebase/cherry-pick/revert operations, phase transitions are skipped entirely.
 //
 //nolint:unparam,maintidx // error return required by interface but hooks must return nil; maintidx: complex but already well-structured
@@ -559,11 +622,8 @@ func (s *ManualCommitStrategy) PostCommit() error {
 		}
 		transitionCtx.HasFilesTouched = len(state.FilesTouched) > 0
 
-		// Run the state machine transition
-		remaining := TransitionAndLog(state, session.EventGitCommit, transitionCtx)
-
-		// Save FilesTouched BEFORE the action loop — condensation clears it,
-		// but we need the original list for carry-forward computation.
+		// Save FilesTouched BEFORE TransitionAndLog — the handler's condensation
+		// clears it, but we need the original list for carry-forward computation.
 		// For mid-session commits (ACTIVE, no shadow branch), state.FilesTouched may be empty
 		// because no SaveChanges/Stop has been called yet. Extract files from transcript.
 		filesTouchedBefore := make([]string, len(state.FilesTouched))
@@ -580,63 +640,28 @@ func (s *ManualCommitStrategy) PostCommit() error {
 			slog.Any("files", filesTouchedBefore),
 		)
 
-		condensed := false
-
-		// Dispatch strategy-specific actions.
-		// Each branch handles its own BaseCommit update so there is no
-		// fallthrough conditional at the end. On condensation failure,
-		// BaseCommit is intentionally NOT updated to preserve access to
-		// the shadow branch (which is named after the old BaseCommit).
-		for _, action := range remaining {
-			switch action {
-			case session.ActionCondense:
-				// For ACTIVE sessions, any commit during the turn is session-related.
-				// For IDLE/ENDED sessions (e.g., carry-forward), also require that the
-				// committed files overlap with the session's remaining files AND have
-				// matching content — otherwise an unrelated commit (or a commit with
-				// completely replaced content) would incorrectly get this session's checkpoint.
-				shouldCondense := hasNew
-				if shouldCondense && !state.Phase.IsActive() {
-					shouldCondense = filesOverlapWithContent(repo, shadowBranchName, commit, state.FilesTouched)
-				}
-				if shouldCondense {
-					condensed = s.condenseAndUpdateState(logCtx, repo, checkpointID, state, head, shadowBranchName, shadowBranchesToDelete, committedFileSet)
-					// condenseAndUpdateState updates BaseCommit on success.
-					// On failure, BaseCommit is preserved so the shadow branch remains accessible.
-				} else {
-					// No new content or unrelated commit — just update BaseCommit
-					s.updateBaseCommitIfChanged(logCtx, state, newHead)
-				}
-			case session.ActionCondenseIfFilesTouched:
-				// The state machine already gates this action on HasFilesTouched,
-				// but hasNew is an additional content-level check (transcript has
-				// new content beyond what was previously condensed).
-				if len(state.FilesTouched) > 0 && hasNew {
-					condensed = s.condenseAndUpdateState(logCtx, repo, checkpointID, state, head, shadowBranchName, shadowBranchesToDelete, committedFileSet)
-					// On failure, BaseCommit is preserved (same as ActionCondense).
-				} else {
-					s.updateBaseCommitIfChanged(logCtx, state, newHead)
-				}
-			case session.ActionDiscardIfNoFiles:
-				if len(state.FilesTouched) == 0 {
-					logging.Debug(logCtx, "post-commit: skipping empty ended session (no files to condense)",
-						slog.String("session_id", state.SessionID),
-					)
-				}
-				s.updateBaseCommitIfChanged(logCtx, state, newHead)
-			case session.ActionClearEndedAt, session.ActionUpdateLastInteraction:
-				// Handled by session.ApplyCommonActions above
-			case session.ActionWarnStaleSession:
-				// Not produced by EventGitCommit; listed for switch exhaustiveness
-			}
+		// Run the state machine transition with handler for strategy-specific actions.
+		handler := &postCommitActionHandler{
+			s:                      s,
+			logCtx:                 logCtx,
+			repo:                   repo,
+			checkpointID:           checkpointID,
+			head:                   head,
+			commit:                 commit,
+			newHead:                newHead,
+			shadowBranchName:       shadowBranchName,
+			shadowBranchesToDelete: shadowBranchesToDelete,
+			committedFileSet:       committedFileSet,
+			hasNew:                 hasNew,
 		}
+		TransitionAndLog(state, session.EventGitCommit, transitionCtx, handler)
 
 		// Record checkpoint ID for ACTIVE sessions so HandleTurnEnd can finalize
 		// with full transcript. IDLE/ENDED sessions already have complete transcripts.
 		// NOTE: This check runs AFTER TransitionAndLog updated the phase. It relies on
 		// ACTIVE + GitCommit → ACTIVE (phase stays ACTIVE). If that state machine
 		// transition ever changed, this guard would silently stop recording IDs.
-		if condensed && state.Phase.IsActive() {
+		if handler.condensed && state.Phase.IsActive() {
 			state.TurnCheckpointIDs = append(state.TurnCheckpointIDs, checkpointID.String())
 		}
 
@@ -645,7 +670,7 @@ func (s *ManualCommitStrategy) PostCommit() error {
 		// commit across two `git commit` invocations, each gets a 1:1 checkpoint.
 		// Uses content-aware comparison: if user did `git add -p` and committed
 		// partial changes, the file still has remaining agent changes to carry forward.
-		if condensed {
+		if handler.condensed {
 			remainingFiles := filesWithRemainingAgentChanges(repo, shadowBranchName, commit, filesTouchedBefore, committedFileSet)
 			logging.Debug(logCtx, "post-commit: carry-forward decision (content-aware)",
 				slog.String("session_id", state.SessionID),
@@ -666,7 +691,7 @@ func (s *ManualCommitStrategy) PostCommit() error {
 
 		// Only preserve shadow branch for active sessions that were NOT condensed.
 		// Condensed sessions already have their data on entire/checkpoints/v1.
-		if state.Phase.IsActive() && !condensed {
+		if state.Phase.IsActive() && !handler.condensed {
 			uncondensedActiveOnBranch[shadowBranchName] = true
 		}
 	}
@@ -1256,7 +1281,7 @@ func (s *ManualCommitStrategy) InitializeSession(sessionID string, agentType age
 
 	if state != nil && state.BaseCommit != "" {
 		// Session is fully initialized — apply phase transition for TurnStart
-		TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{})
+		TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{})
 
 		// Generate a new TurnID for each turn (correlates carry-forward checkpoints)
 		turnID, err := id.Generate()
@@ -1315,7 +1340,7 @@ func (s *ManualCommitStrategy) InitializeSession(sessionID string, agentType age
 	}
 
 	// Apply phase transition: new session starts as ACTIVE
-	TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{})
+	TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{})
 
 	// Calculate attribution for pre-prompt edits
 	// This captures any user edits made before the first prompt
diff --git a/cmd/entire/cli/strategy/phase_postcommit_test.go b/cmd/entire/cli/strategy/phase_postcommit_test.go
index d321ca34f..db46f61fe 100644
--- a/cmd/entire/cli/strategy/phase_postcommit_test.go
+++ b/cmd/entire/cli/strategy/phase_postcommit_test.go
@@ -639,11 +639,10 @@ func TestTurnEnd_Active_NoActions(t *testing.T) {
 
 	// ACTIVE + TurnEnd → IDLE with no strategy-specific actions
 	result := session.Transition(state.Phase, session.EventTurnEnd, session.TransitionContext{})
-	remaining := session.ApplyCommonActions(state, result)
 
-	// Verify no strategy-specific actions for ACTIVE → IDLE
-	assert.Empty(t, remaining,
-		"ACTIVE + TurnEnd should not emit strategy-specific actions")
+	// Apply transition with no-op handler (no strategy actions for ACTIVE → IDLE)
+	err = session.ApplyTransition(state, result, session.NoOpActionHandler{})
+	require.NoError(t, err)
 
 	// Call HandleTurnEnd — should be a no-op (no TurnCheckpointIDs)
 	err = s.HandleTurnEnd(state)
diff --git a/cmd/entire/cli/strategy/session_state.go b/cmd/entire/cli/strategy/session_state.go
index 9d9a3b18b..71f1f1ae0 100644
--- a/cmd/entire/cli/strategy/session_state.go
+++ b/cmd/entire/cli/strategy/session_state.go
@@ -167,16 +167,23 @@ func FindMostRecentSession() string {
 	return ""
 }
 
-// TransitionAndLog runs a session phase transition, applies common actions, logs the
-// transition, and returns any remaining strategy-specific actions.
+// TransitionAndLog runs a session phase transition, applies actions via the
+// handler, and logs the transition.
 // This is the single entry point for all state machine transitions to ensure
 // consistent logging of phase changes.
-func TransitionAndLog(state *SessionState, event session.Event, ctx session.TransitionContext) []session.Action {
+func TransitionAndLog(state *SessionState, event session.Event, ctx session.TransitionContext, handler session.ActionHandler) {
 	oldPhase := state.Phase
 	result := session.Transition(oldPhase, event, ctx)
-	remaining := session.ApplyCommonActions(state, result)
-
 	logCtx := logging.WithComponent(context.Background(), "session")
+
+	if err := session.ApplyTransition(state, result, handler); err != nil {
+		logging.Error(logCtx, "action handler error during transition",
+			slog.String("session_id", state.SessionID),
+			slog.String("event", event.String()),
+			slog.Any("error", err),
+		)
+	}
+
 	if result.NewPhase != oldPhase {
 		logging.Info(logCtx, "phase transition",
 			slog.String("session_id", state.SessionID),
@@ -191,8 +198,6 @@ func TransitionAndLog(state *SessionState, event session.Event, ctx session.Tran
 			slog.String("phase", string(result.NewPhase)),
 		)
 	}
-
-	return remaining
 }
 
 // ClearSessionState removes the session state file for the given session ID.
diff --git a/cmd/entire/cli/strategy/session_state_test.go b/cmd/entire/cli/strategy/session_state_test.go
index 0275977e9..b20856e16 100644
--- a/cmd/entire/cli/strategy/session_state_test.go
+++ b/cmd/entire/cli/strategy/session_state_test.go
@@ -1,10 +1,12 @@
 package strategy
 
 import (
+	"errors"
 	"os"
 	"testing"
 	"time"
 
+	"github.com/entireio/cli/cmd/entire/cli/session"
 	"github.com/go-git/go-git/v5"
 )
 
@@ -380,3 +382,32 @@ func TestFindMostRecentSession_FallsBackWhenNoWorktreeMatch(t *testing.T) {
 		t.Logf("cleanup warning: %v", err)
 	}
 }
+
+// errorActionHandler returns an error from HandleCondense to test
+// that TransitionAndLog continues despite handler errors.
+type errorActionHandler struct {
+	session.NoOpActionHandler
+}
+
+func (errorActionHandler) HandleCondense(_ *session.State) error {
+	return errors.New("test condense error")
+}
+
+// TestTransitionAndLog_ContinuesDespiteHandlerError verifies that TransitionAndLog
+// applies the phase transition even when the handler returns an error.
+func TestTransitionAndLog_ContinuesDespiteHandlerError(t *testing.T) {
+	t.Parallel()
+
+	state := &SessionState{
+		SessionID: "test-error-handler",
+		Phase:     session.PhaseActiveCommitted,
+	}
+
+	// ACTIVE_COMMITTED + TurnEnd → IDLE with ActionCondense.
+	// The handler will fail on ActionCondense, but the phase should still be IDLE.
+	TransitionAndLog(state, session.EventTurnEnd, session.TransitionContext{}, &errorActionHandler{})
+
+	if state.Phase != session.PhaseIdle {
+		t.Errorf("Phase = %q, want %q (should transition despite handler error)", state.Phase, session.PhaseIdle)
+	}
+}
diff --git a/cmd/entire/cli/strategy/strategy.go b/cmd/entire/cli/strategy/strategy.go
index 7866a74fc..9f1a8fa1b 100644
--- a/cmd/entire/cli/strategy/strategy.go
+++ b/cmd/entire/cli/strategy/strategy.go
@@ -464,7 +464,7 @@ type PrePushHandler interface {
 type TurnEndHandler interface {
 	// HandleTurnEnd performs strategy-specific cleanup at the end of a turn.
 	// Work items are read from state (e.g. TurnCheckpointIDs), not from the
-	// action list. The state has already been updated by ApplyCommonActions;
+	// action list. The state has already been updated by ApplyTransition;
 	// the caller saves it after this method returns.
 	HandleTurnEnd(state *session.State) error
 }

From 99d5ec3e384d9711335af8555ae4b3deb8efa181 Mon Sep 17 00:00:00 2001
From: Peyton Montei <peyton@entire.io>
Date: Fri, 13 Feb 2026 17:36:37 -0800
Subject: [PATCH 2/2] Ensure common actions always run and propagate handler
 errors

---
 cmd/entire/cli/hooks.go                       |  4 +-
 cmd/entire/cli/hooks_claudecode_handlers.go   |  8 +++-
 cmd/entire/cli/session/phase.go               | 45 +++++++++++++------
 cmd/entire/cli/session/phase_test.go          | 26 ++++++++++-
 .../cli/strategy/manual_commit_hooks.go       | 19 +++++---
 cmd/entire/cli/strategy/session_state.go      | 16 +++++--
 cmd/entire/cli/strategy/session_state_test.go | 18 +++++---
 7 files changed, 101 insertions(+), 35 deletions(-)

diff --git a/cmd/entire/cli/hooks.go b/cmd/entire/cli/hooks.go
index 1356f9733..1faa6bccb 100644
--- a/cmd/entire/cli/hooks.go
+++ b/cmd/entire/cli/hooks.go
@@ -284,7 +284,9 @@ func handleSessionStartCommon() error {
 	if state, loadErr := strategy.LoadSessionState(input.SessionID); loadErr != nil {
 		fmt.Fprintf(os.Stderr, "Warning: failed to load session state on start: %v\n", loadErr)
 	} else if state != nil {
-		strategy.TransitionAndLog(state, session.EventSessionStart, session.TransitionContext{}, session.NoOpActionHandler{})
+		if transErr := strategy.TransitionAndLog(state, session.EventSessionStart, session.TransitionContext{}, session.NoOpActionHandler{}); transErr != nil {
+			fmt.Fprintf(os.Stderr, "Warning: session start transition failed: %v\n", transErr)
+		}
 		if saveErr := strategy.SaveSessionState(state); saveErr != nil {
 			fmt.Fprintf(os.Stderr, "Warning: failed to update session state on start: %v\n", saveErr)
 		}
diff --git a/cmd/entire/cli/hooks_claudecode_handlers.go b/cmd/entire/cli/hooks_claudecode_handlers.go
index 9d084d893..c72ba5364 100644
--- a/cmd/entire/cli/hooks_claudecode_handlers.go
+++ b/cmd/entire/cli/hooks_claudecode_handlers.go
@@ -748,7 +748,9 @@ func transitionSessionTurnEnd(sessionID string) {
 	if turnState == nil {
 		return
 	}
-	strategy.TransitionAndLog(turnState, session.EventTurnEnd, session.TransitionContext{}, session.NoOpActionHandler{})
+	if err := strategy.TransitionAndLog(turnState, session.EventTurnEnd, session.TransitionContext{}, session.NoOpActionHandler{}); err != nil {
+		fmt.Fprintf(os.Stderr, "Warning: turn-end transition failed: %v\n", err)
+	}
 
 	// Always dispatch to strategy for turn-end handling. The strategy reads
 	// work items from state (e.g. TurnCheckpointIDs), not the action list.
@@ -774,7 +776,9 @@ func markSessionEnded(sessionID string) error {
 		return nil // No state file, nothing to update
 	}
 
-	strategy.TransitionAndLog(state, session.EventSessionStop, session.TransitionContext{}, session.NoOpActionHandler{})
+	if transErr := strategy.TransitionAndLog(state, session.EventSessionStop, session.TransitionContext{}, session.NoOpActionHandler{}); transErr != nil {
+		fmt.Fprintf(os.Stderr, "Warning: session stop transition failed: %v\n", transErr)
+	}
 
 	now := time.Now()
 	state.EndedAt = &now
diff --git a/cmd/entire/cli/session/phase.go b/cmd/entire/cli/session/phase.go
index dda33769a..500fb076e 100644
--- a/cmd/entire/cli/session/phase.go
+++ b/cmd/entire/cli/session/phase.go
@@ -267,41 +267,58 @@ func (NoOpActionHandler) HandleCondenseIfFilesTouched(_ *State) error { return n
 func (NoOpActionHandler) HandleDiscardIfNoFiles(_ *State) error       { return nil }
 func (NoOpActionHandler) HandleWarnStaleSession(_ *State) error       { return nil }
 
-// ApplyTransition applies a TransitionResult to state: sets the new phase,
-// handles common actions internally, and calls the ActionHandler for
-// strategy-specific actions. Returns on the first handler error, leaving
-// subsequent actions unexecuted.
+// ApplyTransition applies a TransitionResult to state: sets the new phase
+// unconditionally, then executes all actions. Common actions
+// (UpdateLastInteraction, ClearEndedAt) always run regardless of handler
+// errors so that bookkeeping fields stay consistent with the new phase.
+// Strategy-specific handler actions stop on the first error; subsequent
+// handler actions are skipped but common actions continue. Returns the
+// first handler error, or nil.
 func ApplyTransition(state *State, result TransitionResult, handler ActionHandler) error {
 	state.Phase = result.NewPhase
 
+	var handlerErr error
 	for _, action := range result.Actions {
 		switch action {
+		// Common actions: always applied, even after a handler error.
 		case ActionUpdateLastInteraction:
 			now := time.Now()
 			state.LastInteractionTime = &now
 		case ActionClearEndedAt:
 			state.EndedAt = nil
+
+		// Strategy-specific actions: skip remaining after the first handler error.
 		case ActionCondense:
-			if err := handler.HandleCondense(state); err != nil {
-				return fmt.Errorf("%s: %w", action, err)
+			if handlerErr == nil {
+				if err := handler.HandleCondense(state); err != nil {
+					handlerErr = fmt.Errorf("%s: %w", action, err)
+				}
 			}
 		case ActionCondenseIfFilesTouched:
-			if err := handler.HandleCondenseIfFilesTouched(state); err != nil {
-				return fmt.Errorf("%s: %w", action, err)
+			if handlerErr == nil {
+				if err := handler.HandleCondenseIfFilesTouched(state); err != nil {
+					handlerErr = fmt.Errorf("%s: %w", action, err)
+				}
 			}
 		case ActionDiscardIfNoFiles:
-			if err := handler.HandleDiscardIfNoFiles(state); err != nil {
-				return fmt.Errorf("%s: %w", action, err)
+			if handlerErr == nil {
+				if err := handler.HandleDiscardIfNoFiles(state); err != nil {
+					handlerErr = fmt.Errorf("%s: %w", action, err)
+				}
 			}
 		case ActionWarnStaleSession:
-			if err := handler.HandleWarnStaleSession(state); err != nil {
-				return fmt.Errorf("%s: %w", action, err)
+			if handlerErr == nil {
+				if err := handler.HandleWarnStaleSession(state); err != nil {
+					handlerErr = fmt.Errorf("%s: %w", action, err)
+				}
 			}
 		default:
-			return fmt.Errorf("unhandled action: %s", action)
+			if handlerErr == nil {
+				handlerErr = fmt.Errorf("unhandled action: %s", action)
+			}
 		}
 	}
-	return nil
+	return handlerErr
 }
 
 // MermaidDiagram generates a Mermaid state diagram from the transition table.
diff --git a/cmd/entire/cli/session/phase_test.go b/cmd/entire/cli/session/phase_test.go
index 60c022aba..181d0bac8 100644
--- a/cmd/entire/cli/session/phase_test.go
+++ b/cmd/entire/cli/session/phase_test.go
@@ -516,11 +516,12 @@ func TestApplyTransition_ClearsEndedAt(t *testing.T) {
 	assert.Nil(t, state.EndedAt)
 }
 
-func TestApplyTransition_ReturnsHandlerError(t *testing.T) {
+func TestApplyTransition_ReturnsHandlerError_ButRunsCommonActions(t *testing.T) {
 	t.Parallel()
 
 	state := &State{Phase: PhaseActive}
 	handler := &mockActionHandler{returnErr: errors.New("condense failed")}
+	// Synthetic transition with [Condense, UpdateLastInteraction] actions.
 	result := TransitionResult{
 		NewPhase: PhaseIdle,
 		Actions:  []Action{ActionCondense, ActionUpdateLastInteraction},
@@ -531,6 +532,9 @@ func TestApplyTransition_ReturnsHandlerError(t *testing.T) {
 	require.Error(t, err)
 	assert.Contains(t, err.Error(), "condense failed")
 	assert.Equal(t, PhaseIdle, state.Phase)
+	// Common action must still run even though handler failed.
+	require.NotNil(t, state.LastInteractionTime,
+		"UpdateLastInteraction must run despite earlier handler error")
 }
 
 func TestApplyTransition_StopsOnFirstHandlerError(t *testing.T) {
@@ -549,3 +553,23 @@ func TestApplyTransition_StopsOnFirstHandlerError(t *testing.T) {
 	assert.True(t, handler.condenseCalled)
 	assert.False(t, handler.warnStaleSessionCalled, "should stop on first error")
 }
+
+func TestApplyTransition_ClearEndedAtRunsDespiteHandlerError(t *testing.T) {
+	t.Parallel()
+
+	endedAt := time.Now().Add(-time.Hour)
+	state := &State{Phase: PhaseEnded, EndedAt: &endedAt}
+	handler := &mockActionHandler{returnErr: errors.New("condense failed")}
+	// Synthetic action list to test the mechanism: no real transition produces
+	// this exact ordering, but it verifies that ClearEndedAt (common) always
+	// runs even when a preceding handler action fails.
+	result := TransitionResult{
+		NewPhase: PhaseEnded,
+		Actions:  []Action{ActionCondenseIfFilesTouched, ActionClearEndedAt},
+	}
+
+	err := ApplyTransition(state, result, handler)
+
+	require.Error(t, err)
+	assert.Nil(t, state.EndedAt, "ClearEndedAt must run despite earlier handler error")
+}
diff --git a/cmd/entire/cli/strategy/manual_commit_hooks.go b/cmd/entire/cli/strategy/manual_commit_hooks.go
index c30ddd62a..0ee6a3287 100644
--- a/cmd/entire/cli/strategy/manual_commit_hooks.go
+++ b/cmd/entire/cli/strategy/manual_commit_hooks.go
@@ -525,9 +525,10 @@ func (h *postCommitActionHandler) HandleWarnStaleSession(_ *session.State) error
 	// Not produced by EventGitCommit; no-op for exhaustiveness.
 	return nil
 }
+
 // During rebase/cherry-pick/revert operations, phase transitions are skipped entirely.
 //
-//nolint:unparam,maintidx // error return required by interface but hooks must return nil; maintidx: complex but already well-structured
+//nolint:unparam // error return required by interface but hooks must return nil
 func (s *ManualCommitStrategy) PostCommit() error {
 	logCtx := logging.WithComponent(context.Background(), "checkpoint")
 
@@ -654,7 +655,9 @@ func (s *ManualCommitStrategy) PostCommit() error {
 			committedFileSet:       committedFileSet,
 			hasNew:                 hasNew,
 		}
-		TransitionAndLog(state, session.EventGitCommit, transitionCtx, handler)
+		if err := TransitionAndLog(state, session.EventGitCommit, transitionCtx, handler); err != nil {
+			fmt.Fprintf(os.Stderr, "[entire] Warning: post-commit action handler error: %v\n", err)
+		}
 
 		// Record checkpoint ID for ACTIVE sessions so HandleTurnEnd can finalize
 		// with full transcript. IDLE/ENDED sessions already have complete transcripts.
@@ -1280,8 +1283,10 @@ func (s *ManualCommitStrategy) InitializeSession(sessionID string, agentType age
 	}
 
 	if state != nil && state.BaseCommit != "" {
-		// Session is fully initialized — apply phase transition for TurnStart
-		TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{})
+		// Session is fully initialized — apply phase transition for TurnStart.
+		if transErr := TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{}); transErr != nil {
+			fmt.Fprintf(os.Stderr, "[entire] Warning: turn start transition failed: %v\n", transErr)
+		}
 
 		// Generate a new TurnID for each turn (correlates carry-forward checkpoints)
 		turnID, err := id.Generate()
@@ -1339,8 +1344,10 @@ func (s *ManualCommitStrategy) InitializeSession(sessionID string, agentType age
 		return fmt.Errorf("failed to initialize session: %w", err)
 	}
 
-	// Apply phase transition: new session starts as ACTIVE
-	TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{})
+	// Apply phase transition: new session starts as ACTIVE.
+	if transErr := TransitionAndLog(state, session.EventTurnStart, session.TransitionContext{}, session.NoOpActionHandler{}); transErr != nil {
+		fmt.Fprintf(os.Stderr, "[entire] Warning: turn start transition failed: %v\n", transErr)
+	}
 
 	// Calculate attribution for pre-prompt edits
 	// This captures any user edits made before the first prompt
diff --git a/cmd/entire/cli/strategy/session_state.go b/cmd/entire/cli/strategy/session_state.go
index 71f1f1ae0..86412a264 100644
--- a/cmd/entire/cli/strategy/session_state.go
+++ b/cmd/entire/cli/strategy/session_state.go
@@ -168,19 +168,22 @@ func FindMostRecentSession() string {
 }
 
 // TransitionAndLog runs a session phase transition, applies actions via the
-// handler, and logs the transition.
+// handler, and logs the transition. Returns the first handler error from
+// ApplyTransition (if any) so callers can surface it. The error is also
+// logged internally for diagnostics.
 // This is the single entry point for all state machine transitions to ensure
 // consistent logging of phase changes.
-func TransitionAndLog(state *SessionState, event session.Event, ctx session.TransitionContext, handler session.ActionHandler) {
+func TransitionAndLog(state *SessionState, event session.Event, ctx session.TransitionContext, handler session.ActionHandler) error {
 	oldPhase := state.Phase
 	result := session.Transition(oldPhase, event, ctx)
 	logCtx := logging.WithComponent(context.Background(), "session")
 
-	if err := session.ApplyTransition(state, result, handler); err != nil {
+	handlerErr := session.ApplyTransition(state, result, handler)
+	if handlerErr != nil {
 		logging.Error(logCtx, "action handler error during transition",
 			slog.String("session_id", state.SessionID),
 			slog.String("event", event.String()),
-			slog.Any("error", err),
+			slog.Any("error", handlerErr),
 		)
 	}
 
@@ -198,6 +201,11 @@ func TransitionAndLog(state *SessionState, event session.Event, ctx session.Tran
 			slog.String("phase", string(result.NewPhase)),
 		)
 	}
+
+	if handlerErr != nil {
+		return fmt.Errorf("transition %s: %w", event, handlerErr)
+	}
+	return nil
 }
 
 // ClearSessionState removes the session state file for the given session ID.
diff --git a/cmd/entire/cli/strategy/session_state_test.go b/cmd/entire/cli/strategy/session_state_test.go
index b20856e16..5c598fa97 100644
--- a/cmd/entire/cli/strategy/session_state_test.go
+++ b/cmd/entire/cli/strategy/session_state_test.go
@@ -384,7 +384,7 @@ func TestFindMostRecentSession_FallsBackWhenNoWorktreeMatch(t *testing.T) {
 }
 
 // errorActionHandler returns an error from HandleCondense to test
-// that TransitionAndLog continues despite handler errors.
+// that TransitionAndLog propagates handler errors while still applying the phase transition.
 type errorActionHandler struct {
 	session.NoOpActionHandler
 }
@@ -393,21 +393,25 @@ func (errorActionHandler) HandleCondense(_ *session.State) error {
 	return errors.New("test condense error")
 }
 
-// TestTransitionAndLog_ContinuesDespiteHandlerError verifies that TransitionAndLog
-// applies the phase transition even when the handler returns an error.
-func TestTransitionAndLog_ContinuesDespiteHandlerError(t *testing.T) {
+// TestTransitionAndLog_ReturnsHandlerError verifies that TransitionAndLog
+// applies the phase transition even when the handler returns an error,
+// and propagates that error to the caller.
+func TestTransitionAndLog_ReturnsHandlerError(t *testing.T) {
 	t.Parallel()
 
 	state := &SessionState{
 		SessionID: "test-error-handler",
-		Phase:     session.PhaseActiveCommitted,
+		Phase:     session.PhaseIdle,
 	}
 
-	// ACTIVE_COMMITTED + TurnEnd → IDLE with ActionCondense.
+	// IDLE + GitCommit → IDLE with ActionCondense.
 	// The handler will fail on ActionCondense, but the phase should still be IDLE.
-	TransitionAndLog(state, session.EventTurnEnd, session.TransitionContext{}, &errorActionHandler{})
+	err := TransitionAndLog(state, session.EventGitCommit, session.TransitionContext{}, &errorActionHandler{})
 
 	if state.Phase != session.PhaseIdle {
 		t.Errorf("Phase = %q, want %q (should transition despite handler error)", state.Phase, session.PhaseIdle)
 	}
+	if err == nil {
+		t.Error("TransitionAndLog() should return handler error")
+	}
 }